Thermal [2+2]-cycloadditions of diphenylketene with aryl- and hetaryl-substituted thioketones

The reaction of diphenylketene (1) with aryl- and hetaryl-substituted thioketones (2) gave the corresponding 3,3,4,4-tetraarylthietan-2-ones (3) in good yields. Remarkably, the reactions with bis-hetaryl-substituted thioketones occurred significantly faster compared with those involving the bis-aryl-substituted thioketones. The structure of compound 3c has been established by X-ray crystallography.

[1]  P. Grzelak,et al.  Hetaryl Thioketones: Synthesis and Selected Reactions , 2014 .

[2]  C. Wentrup,et al.  Reactions of Adamantanethione with Ketenes: Formation of a 1,3,5-Dioxathiane , 2014 .

[3]  Louis C. Morrill,et al.  Lewis Base Catalyzed Asymmetric Formal [2+2] Cycloadditions , 2014 .

[4]  J. Wouters,et al.  Mechanistic insight into the Staudinger reaction catalyzed by N-heterocyclic carbenes. , 2013, Chemistry.

[5]  Christopher M. Rasik,et al.  Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions. , 2013, Journal of the American Chemical Society.

[6]  Lin He,et al.  N-Heterocyclic carbene catalysis: enantioselective formal [2+2] cycloaddition of ketenes and N-sulfinylanilines. , 2011, Angewandte Chemie.

[7]  A. Slawin,et al.  Chiral relay in NHC-mediated asymmetric β-lactam synthesis I; substituent effects in NHCs derived from (1R,2R)-cyclohexane-1,2-diamine , 2010 .

[8]  N. Kerrigan,et al.  Phosphine-catalyzed asymmetric synthesis of beta-lactones from arylketoketenes and aromatic aldehydes. , 2010, Organic letters.

[9]  S. Ye,et al.  Enantioselective Synthesis of Dihydrocoumarins via N‐Heterocyclic Carbene‐Catalyzed Cycloaddition of Ketenes and o‐Quinone Methides , 2009 .

[10]  M. Sakamoto,et al.  SYNTHESIS OF 1,2,4-TRIAZIN-5-ONES THROUGH [4+2] CYCLOADDITION OF 1,2,4-TRIAZA-1,3-DIENES WITH DIPHENYLKETENE , 2009 .

[11]  R. Wilhelm,et al.  Enantiopure imidazolinium-dithiocarboxylates as highly selective novel organocatalysts. , 2009, Chemical communications.

[12]  Takao Saito,et al.  A novel and efficient stereo-controlled synthesis of hexahydroquinolinones via the diene-transmissive hetero-Diels–Alder reaction of cross-conjugated azatrienes with ketenes and electrophilic dienophiles , 2009 .

[13]  M. Sakamoto,et al.  〔4+2〕cycloaddition of diphenylketene to 1-aza-1,3-dienes , 2009 .

[14]  Lin He,et al.  Formal cycloaddition of disubstituted ketenes with 2-oxoaldehydes catalyzed by chiral N-heterocyclic carbenes. , 2008, The Journal of organic chemistry.

[15]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[16]  J. Popp,et al.  Oxidations of sulfur rich heterocycles – new S-oxides of the parent 1,2,4-trithiolane and its tetramethyl derivative: synthesis and structural investigations , 2004 .

[17]  R. Huisgen,et al.  1,3-dithiolanes from cycloadditions of alicyclic and aliphatic thiocarbonyl ylides with thiones: regioselectivity. , 2003, Chemistry.

[18]  T. Lectka,et al.  The development of the first catalyzed reaction of ketenes and imines: catalytic, asymmetric synthesis of beta-lactams. , 2002, Journal of the American Chemical Society.

[19]  H. Heimgartner,et al.  Regioselektive 1,3-Dipolare Cycloadditionen eines ‘Thiocarbonyl-methanids’ ((Alkylidensulfonio)methanids) mit aromatischen Sulfinen , 1996 .

[20]  H. Ulrich Cumulenes in Click Reactions , 1994 .

[21]  E. Vedejs,et al.  Characterization of monomeric thiopivalaldehyde , 1986 .

[22]  L. Toupet,et al.  Des 6H-thiazines-1,3 aux céphèmes par cyclocondensation , 1986 .

[23]  P. Bartlett,et al.  Autoxidation of diphenylketene. 1. Conditions and products , 1983 .

[24]  H. Kohn,et al.  Studies on the reaction of 3,3,4,4-tetraphenylthietan-2-one , 1981 .

[25]  H. Yamaguchi,et al.  Chemistry of .alpha.,.beta.-unsaturated thione dimers. 3. Reactions of thiochalcones and 2-arylidene-1-thiotetralones with cumulenes containing a carbon-carbon double bond , 1980 .

[26]  H. Kohn,et al.  Studies of the reaction of thiocarbonyl-containing compounds with ketenes , 1979 .

[27]  B. Zwanenburg,et al.  Regio- and stereo-specificity of cycloaddition reactions of sulphines with diphenylnitrilimine , 1978 .

[28]  B. Zwanenburg,et al.  Sulphines. Part IV. Reactions of aromatic sulphines with diazoalkanes , 1972 .

[29]  F. Effenberger,et al.  Enoläther, IX. Stereospezifische Cycloaddition von Sulfonylisocyanaten an Enoläther — Konfiguration, Isomerisierung und Umlagerung der Cycloaddukte , 1971 .

[30]  R. Huisgen,et al.  Cycloadditionen der Ketene, I. Diphenylketen und gewöhnliche Alkene , 1969 .

[31]  William T. Simpson,et al.  Coherent X‐Ray Scattering for the Hydrogen Atom in the Hydrogen Molecule , 1965 .

[32]  J. Ibers,et al.  Dispersion corrections and crystal structure refinements , 1964 .

[33]  H. Staudinger Ketene XXXV: Einwirkung von Diphenylketen auf Thioketone , 1920 .

[34]  H. Staudinger Zur Kenntniss der Ketene. Diphenylketen , 1907 .